Water → Hippuric Acid

HRID 1178078Notes

Reaction equation

HRID 1178078 reaction equation
O[Li].O.C([O:6][C:7](=[O:18])[CH2:8][NH:9][C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)C.C1COCC1.O>CO>[C:10]([NH:9][CH2:8][C:7]([OH:18])=[O:6])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 226558Ethyl Hippurate

Product 1

HCID 464Hippuric AcidYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

LiOH.H2O (73 mg, 1.74 mmol) was added to a solution of benzoylamino-acetic acid ethyl ester (90 mg, 0.43 mmol) in a mixture of MeOH (5 mL), THF (2 mL) and H2O (2 mL). The resulting mixture was stirred for 3 hrs at room temperature. The MeOH and THF were evaporated and the resulting residue was diluted with water (2 mL), acidified with citric acid and extracted with EtOAc. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated under reduced pressure to afford benzoylamino-acetic acid in 77% yield. LC-MS purity: 92%

Workup

  1. customThe MeOH and THF were evaporated
  2. additionthe resulting residue was diluted with water (2 mL)
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0195983658a24c2b9be6da9f15f4c842
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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